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5.1.99.4: alpha-methylacyl-CoA racemase

This is an abbreviated version!
For detailed information about alpha-methylacyl-CoA racemase, go to the full flat file.

Word Map on EC 5.1.99.4

Reaction

(2S)-2-methylacyl-CoA
=
(2R)-2-methylacyl-CoA

Synonyms

2-arylpropionyl-CoA epimerase, 2-methylacyl-CoA racemase, alpha-methyl CoA racemase, alpha-Methylacyl CoA racemase, alpha-methylacyl coenzyme A racemase, alpha-methylacyl-CoA racemase, alpha-methylacyl-CoA racemase 1A, alpha-methylacyl-coenzyme A racemase, AMACR, AMACR 1A, AMACR IA, amacr/P504S, GenBank U89905-derived protein GI2145184, GenBank U89906-derived protein GI 2145186, ibuprofenoyl-CoA epimerase, MCR, P504S, Racemase, alpha-methylacyl coenzyme A, Racemase, alpha-methylacyl coenzyme A (Mus musculus clone 3), Racemase, alpha-methylacyl coenzyme A (Rattus norvegicus clone 11)

ECTree

     5 Isomerases
         5.1 Racemases and epimerases
             5.1.99 Acting on other compounds
                5.1.99.4 alpha-methylacyl-CoA racemase

Reference

topprint

Reference on EC 5.1.99.4 - alpha-methylacyl-CoA racemase

Please use the Reference Search for a specific query.
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REF.
AUTHORS
TITLE
JOURNAL
VOL.
PAGES
YEAR
ORGANISM (UNIPROT)
PUBMED ID
SOURCE
Schmitz, W.; Fingerhut, R.; Conzelmann, E.
Purification and properties of an alpha-methylacyl-CoA racemase from rat liver
Eur. J. Biochem.
222
313-323
1994
Rattus norvegicus
Manually annotated by BRENDA team
Schmitz, W.; Albers, C.; Fingerhut, R.; Conzelmann, E.
Purification and characterization of an alpha-methylacyl-CoA racemase from human liver
Eur. J. Biochem.
231
815-822
1995
Homo sapiens, Rattus norvegicus
Manually annotated by BRENDA team
Schmitz, W.; Helander, H.M.; Hiltunen, J.K.; Conzelmann, E.
Molecular cloning of cDNA species for rat and mouse liver alpha-methylacyl-CoA racemase
Biochem. J.
326
883-889
1997
Mus musculus (O09174), Mus musculus, Rattus norvegicus (P70473)
Manually annotated by BRENDA team
Van Veldhoven, P.P.; Croes, K.; Casteels, M.; Mannaerts, G.P.
2-Methylacyl racemase: a coupled assay based on the use of pristanoyl-CoA oxidase/peroxidase and reinvestigation of its subcellular distribution in rat and human liver
Biochim. Biophys. Acta
1347
62-68
1997
Homo sapiens, Rattus norvegicus
Manually annotated by BRENDA team
Bhaumik, P.; Kursula, P.; Ratas, V.; Conzelmann, E.; Hiltunen, J.K.; Schmitz, W.; Wierenga, R.K.
Crystallization and preliminary X-ray diffraction studies of an alpha-methylacyl-CoA racemase from Mycobacterium tuberculosis
Acta Crystallogr. Sect. D
59
353-355
2003
Mycobacterium tuberculosis
Manually annotated by BRENDA team
Cuebas, D.A.; Phillips, C.; Schmitz, W.; Conzelmann, E.; Novikov, D.K.
The role of alpha-methylacyl-CoA racemase in bile acid synthesis
Biochem. J.
363
801-807
2002
Rattus norvegicus
Manually annotated by BRENDA team
Kumar-Sinha, C.; Shah, R.B.; Laxman, B.; Tomlins, S.A.; Harwood, J.; Schmitz, W.; Conzelmann, E.; Sanda, M.G.; Wei, J.T.; Rubin, M.A.; Chinnaiyan, A.M.
Elevated alpha-methylacyl-CoA racemase enzymatic activity in prostate cancer
Am. J. Pathol.
164
787-793
2004
Homo sapiens
Manually annotated by BRENDA team
Mubiru, J.N.; Shen-Ong, G.L.; Valente, A.J.; Troyer, D.A.
Alternative spliced variants of the alpha-methylacyl-CoA racemase gene and their expression in prostate cancer
Gene
327
89-98
2004
Homo sapiens (B3KMU8), Homo sapiens (Q6VRU3), Homo sapiens (Q6VRU4), Homo sapiens (Q9UHK6), Homo sapiens
Manually annotated by BRENDA team
Sakai, Y.; Takahashi, H.; Wakasa, Y.; Kotani, T.; Yurimoto, H.; Miyachi, N.; Van Veldhoven, P.P.; Kato, N.
Role of alpha-methylacyl coenzyme A racemase in the degradation of methyl-branched alkanes by Mycobacterium sp. strain P101
J. Bacteriol.
186
7214-7220
2004
Mycobacterium sp., Mycobacterium sp. P101
Manually annotated by BRENDA team
Savolainen, K.; Bhaumik, P.; Schmitz, W.; Kotti, T.J.; Conzelmann, E.; Wierenga, R.K.; Hiltunen, J.K.
alpha-Methylacyl-CoA racemase from Mycobacterium tuberculosis. Mutational and structural characterization of the active site and the fold
J. Biol. Chem.
280
12611-12620
2005
Mycobacterium tuberculosis
Manually annotated by BRENDA team
Ananthanarayanan, V.; Deaton, R.J.; Yang, X.J.; Pins, M.R.; Gann, P.H.
Alpha-methylacyl-CoA racemase (AMACR) expression in normal prostatic glands and high-grade prostatic intraepithelial neoplasia (HGPIN): association with diagnosis of prostate cancer
Prostate
63
341-346
2005
Homo sapiens
Manually annotated by BRENDA team
Mubiru, J.N.; Valente, A.J.; Troyer, D.A.
A variant of the alpha-methyl-acyl-CoA racemase gene created by a deletion in exon 5 and its expression in prostate cancer
Prostate
65
117-123
2005
Homo sapiens (Q9UHK6)
Manually annotated by BRENDA team
Langner, C.; Rupar, G.
Alpha-methylacyl-CoA racemase (AMACR/P504S) protein expression in urothelial carcinoma of the upper urinary tract correlates with tumour progression
Virchows Arch.
448
325-330
2006
Homo sapiens
Manually annotated by BRENDA team
Mayes, D.C.; Patterson, J.W.; Ramnani, D.M.; Mills, S.E.
alpha-Methylacyl coenzyme A racemase is immunoreactive in extramammary Paget disease
Am. J. Clin. Pathol.
127
567-571
2007
Homo sapiens
Manually annotated by BRENDA team
Santinelli, A.; Mazzucchelli, R.; Barbisan, F.; Lopez-Beltran, A.; Cheng, L.; Scarpelli, M.; Montironi, R.
alpha-Methylacyl coenzyme A racemase, Ki-67, and topoisomerase IIalpha in cystoprostatectomies with incidental prostate cancer
Am. J. Clin. Pathol.
128
657-666
2007
Homo sapiens
Manually annotated by BRENDA team
Guzman, G.; Wu, S.J.; Kajdacsy-Balla, A.; Cotler, S.J.
alpha-Methylacyl-CoA racemase (AMACR/P504S) can distinguish hepatocellular carcinoma and dysplastic hepatocytes from benign nondysplastic hepatocytes
Appl. Immunohistochem. Mol. Morphol.
14
411-416
2006
Homo sapiens
Manually annotated by BRENDA team
Shi, X.; Gong, E.; Wu, X.
alpha-Methylacyl-CoA racemase/P504S overexpression in colorectal carcinoma is correlated with tumor differentiation
Appl. Immunohistochem. Mol. Morphol.
15
175-180
2007
Homo sapiens
Manually annotated by BRENDA team
Shilo, K.; Dracheva, T.; Mani, H.; Fukuoka, J.; Sesterhenn, I.A.; Chu, W.S.; Shih, J.H.; Jen, J.; Travis, W.D.; Franks, T.J.
Alpha-methylacyl CoA racemase in pulmonary adenocarcinoma, squamous cell carcinoma, and neuroendocrine tumors: expression and survival analysis
Arch. Pathol. Lab. Med.
131
1555-1560
2007
Homo sapiens
Manually annotated by BRENDA team
Carswell, B.M.; Woda, B.A.; Wang, X.; Li, C.; Dresser, K.; Jiang, Z.
Detection of prostate cancer by alpha-methylacyl CoA racemase (P504S) in needle biopsy specimens previously reported as negative for malignancy
Histopathology
48
668-673
2006
Homo sapiens
Manually annotated by BRENDA team
Lisovsky, M.; Falkowski, O.; Bhuiya, T.
Expression of alpha-methylacyl-coenzyme A racemase in dysplastic Barretts epithelium
Hum. Pathol.
37
1601-1606
2006
Homo sapiens
Manually annotated by BRENDA team
Molinie, V.; Balaton, A.; Rotman, S.; Mansouri, D.; De Pinieux, I.; Homsi, T.; Guillou, L.
alpha-Methyl CoA racemase expression in renal cell carcinomas
Hum. Pathol.
37
698-703
2006
Homo sapiens
Manually annotated by BRENDA team
Sung, M.T.; Jiang, Z.; Montironi, R.; MacLennan, G.T.; Mazzucchelli, R.; Cheng, L.
alpha-Methylacyl-CoA racemase (P504S)/34betaE12/p63 triple cocktail stain in prostatic adenocarcinoma after hormonal therapy
Hum. Pathol.
38
332-341
2007
Homo sapiens
Manually annotated by BRENDA team
Lin, A.; Weiser, M.R.; Klimstra, D.S.; Paty, P.B.; Tang, L.H.; Al-Ahmadie, H.; Hoo Park, S.; Guillem, J.G.; Temple, L.; Wong, W.D.; Gerald, W.L.; Shia, J.
Differential expression of alpha-methylacyl-coenzyme A racemase in colorectal carcinoma bears clinical and pathologic significance
Hum. Pathol.
38
850-856
2007
Homo sapiens
Manually annotated by BRENDA team
Carnell, A.J.; Hale, I.; Denis, S.; Wanders, R.J.; Isaacs, W.B.; Wilson, B.A.; Ferdinandusse, S.
Design, synthesis, and in vitro testing of alpha-methylacyl-CoA racemase inhibitors
J. Med. Chem.
50
2700-2707
2007
Rattus norvegicus
Manually annotated by BRENDA team
Bhaumik, P.; Schmitz, W.; Hassinen, A.; Hiltunen, J.K.; Conzelmann, E.; Wierenga, R.K.
The catalysis of the 1,1-proton transfer by alpha-methyl-acyl-CoA racemase is coupled to a movement of the fatty acyl moiety over a hydrophobic, methionine-rich surface
J. Mol. Biol.
367
1145-1161
2007
Mycobacterium tuberculosis (O06543), Mycobacterium tuberculosis
Manually annotated by BRENDA team
Olgac, S.; Hutchinson, B.; Tickoo, S.K.; Reuter, V.E.
alpha-Methylacyl-CoA racemase as a marker in the differential diagnosis of metanephric adenoma
Mod. Pathol.
19
218-224
2006
Homo sapiens
Manually annotated by BRENDA team
Lee, W.A.
alpha-Methylacyl-CoA-racemase expression in adenocarcinoma, dysplasia and non-neoplastic epithelium of the stomach
Oncology
71
246-250
2006
Homo sapiens
Manually annotated by BRENDA team
Daugherty, S.E.; Shugart, Y.Y.; Platz, E.A.; Fallin, M.D.; Isaacs, W.B.; Pfeiffer, R.M.; Welch, R.; Huang, W.Y.; Reding, D.; Hayes, R.B.
Polymorphic variants in alpha-methylacyl-CoA racemase and prostate cancer
Prostate
67
1487-1497
2007
Homo sapiens
Manually annotated by BRENDA team
Levin, A.M.; Zuhlke, K.A.; Ray, A.M.; Cooney, K.A.; Douglas, J.A.
Sequence variation in alpha-methylacyl-CoA racemase and risk of early-onset and familial prostate cancer
Prostate
67
1507-1513
2007
Homo sapiens
Manually annotated by BRENDA team
Huang, W.; Zhao, J.; Li, L.; Huang, Y.; Yang, X.; Wang, J.; Zhang, T.
a-Methylacyl coenzyme A racemase is highly expressed in the intestinal-type adenocarcinoma and high-grade dysplasia lesions of the stomach
Histol. Histopathol.
23
1315-1320
2008
Homo sapiens
Manually annotated by BRENDA team
Scheil-Bertram, S.; Lorenz, D.; Ell, C.; Sheremet, E.; Fisseler-Eckhoff, A.
Expression of alpha-methylacyl coenzyme A racemase in the dysplasia carcinoma sequence associated with Barretts esophagus
Mod. Pathol.
21
961-967
2008
Homo sapiens
Manually annotated by BRENDA team
Gunia, S.; May, M.; Scholmann, K.; Stoerkel, S.; Hoschke, B.; Koch, S.; Dietel, M.; Kristiansen, G.
Expression of alpha-methylacyl-CoA racemase correlates with histopathologic grading in noninvasive bladder cancer
Virchows Arch.
453
165-170
2008
Homo sapiens
Manually annotated by BRENDA team
Trpkov, K.; Bartczak-McKay, J.; Yilmaz, A.
Usefulness of cytokeratin 5/6 and AMACR applied as double sequential immunostains for diagnostic assessment of problematic prostate specimens
Am. J. Clin. Pathol.
132; 211-20
307
2009
Homo sapiens
Manually annotated by BRENDA team
Ouazia, D.; Bearne, S.L.
A continuous assay for alpha-methylacyl-coenzyme A racemase using circular dichroism
Anal. Biochem.
398
45-51
2010
Mycobacterium tuberculosis
Manually annotated by BRENDA team
Worschech, A.; Meirelles, L.; Billis, A.
Expression of alpha-methylacyl coenzyme a racemase in partial and complete focal atrophy on prostate needle biopsies
Anal. Quant. Cytol. Histol.
31
424-431
2009
Homo sapiens (Q9UHK6)
Manually annotated by BRENDA team
Kaic, G.; Tomasovic-Loncaric, C.
alpha-methylacyl-CoA racemase (AMACR) in fine-needle aspiration specimens of prostate lesions
Diagn. Cytopathol.
37
803-808
2009
Homo sapiens
Manually annotated by BRENDA team
Marx, A.; Wandrey, T.; Simon, P.; Wewer, A.; Grob, T.; Reichelt, U.; Minner, S.; Simon, R.; Spehlmann, M.; Tigges, W.; Soehendra, N.; Seitz, U.; Seewald, S.; Izbicki, J.; Yekebas, E.; Kaifi, J.; Mirlacher, M.; Terracciano, L.; Fleischmann, A.; Raedler, A.
Combined alpha-methylacyl coenzyme A racemase/p53 analysis to identify dysplasia in inflammatory bowel disease
Hum. Pathol.
40
166-173
2009
Homo sapiens
Manually annotated by BRENDA team
Halsey, M.A.; Calder, K.B.; Mathew, R.; Schlauder, S.; Morgan, M.B.
Expression of alpha-methylacyl-CoA racemase (P504S) in sebaceous neoplasms
J. Cutan. Pathol.
37
446-451
2010
Homo sapiens
Manually annotated by BRENDA team
Honma, I.; Torigoe, T.; Hirohashi, Y.; Kitamura, H.; Sato, E.; Masumori, N.; Tamura, Y.; Tsukamoto, T.; Sato, N.
Aberrant expression and potency as a cancer immunotherapy target of alpha-methylacyl-coenzyme A racemase in prostate cancer
J. Transl. Med.
7
103
2009
Homo sapiens
Manually annotated by BRENDA team
Darley, D.J.; Butler, D.S.; Prideaux, S.J.; Thornton, T.W.; Wilson, A.D.; Woodman, T.J.; Threadgill, M.D.; Lloyd, M.D.
Synthesis and use of isotope-labelled substrates for a mechanistic study on human alpha-methylacyl-CoA racemase 1A (AMACR; P504S)
Org. Biomol. Chem.
7
543-552
2009
Homo sapiens (Q9UHK6), Homo sapiens
Manually annotated by BRENDA team
Sattar, F.A.; Darley, D.J.; Politano, F.; Woodman, T.J.; Threadgill, M.D.; Lloyd, M.D.
Unexpected stereoselective exchange of straight-chain fatty acyl-CoA alpha-protons by human alpha-methylacyl-CoA racemase 1A (P504S)
Chem. Commun. (Camb. )
46
3348-3350
2010
Homo sapiens
Manually annotated by BRENDA team
Woodman, T.J.; Wood, P.J.; Thompson, A.S.; Hutchings, T.J.; Steel, G.R.; Jiao, P.; Threadgill, M.D.; Lloyd, M.D.
Chiral inversion of 2-arylpropionyl-CoA esters by human alpha-methylacyl-CoA racemase 1A (P504S)-a potential mechanism for the anti-cancer effects of ibuprofen
Chem. Commun. (Camb. )
47
7332-7334
2011
Homo sapiens
Manually annotated by BRENDA team
Ouyang, B.; Leung, Y.K.; Wang, V.; Chung, E.; Levin, L.; Bracken, B.; Cheng, L.; Ho, S.M.
alpha-Methylacyl-CoA racemase spliced variants and their expression in normal and malignant prostate tissues
Urology
77
2491-2497
2011
Homo sapiens (Q9UHK6)
Manually annotated by BRENDA team
Noske, A.; Zimmermann, A.K.; Caduff, R.; Varga, Z.; Fink, D.; Moch, H.; Kristiansen, G.
Alpha-methylacyl-CoA racemase (AMACR) expression in epithelial ovarian cancer
Virchows Arch.
459
91-97
2011
Homo sapiens
Manually annotated by BRENDA team
Morgenroth, A.; Urusova, E.A.; Dinger, C.; Al-Momani, E.; Kull, T.; Glatting, G.; Frauendorf, H.; Jahn, O.; Mottaghy, F.M.; Reske, S.N.; Zlatopolskiy, B.D.
New molecular markers for prostate tumor imaging: a study on 2-methylene substituted fatty acids as new AMACR inhibitors
Chemistry
17
10144-10150
2011
Rattus norvegicus, Homo sapiens (Q9UHK6)
Manually annotated by BRENDA team
Carnell, A.; Kirk, R.; Smith, M.; Mckenna, S.; Lian, L.; Gibson, R.
Inhibition of human alpha-methylacyl CoA racemase (AMACR): A target for prostate cancer
ChemMedChem
8
1643-1647
2013
Homo sapiens (Q9UHK6), Homo sapiens
Manually annotated by BRENDA team
Sekine, S.; Ogawa, R.; Ojima, H.; Kanai, Y.
Overexpression of alpha-methylacyl-CoA racemase is associated with CTNNB1 mutations in hepatocellular carcinomas
Histopathology
58
712-719
2011
Homo sapiens (Q9UHK6)
Manually annotated by BRENDA team
Annenkov, A.; Nishikura, K.; Domori, K.; Ajioka, Y.
Alpha-methylacyl-coenzyme A racemase expression in neuroendocrine neoplasms of the stomach
Virchows Arch.
461
169-175
2012
Homo sapiens
Manually annotated by BRENDA team
Festuccia, C.; Gravina, G.L.; Mancini, A.; Muzi, P.; Cesare, E.D.; Kirk, R.; Smith, M.; Hughes, S.; Gibson, R.; Lian, L.Y.; Ricevuto, E.; Carnell, A.J.
Trifluoroibuprofen inhibits alpha-methylacyl coenzyme A racemase (AMACR/P504S), reduces cancer cell proliferation and inhibits in vivo tumor growth in aggressive prostate cancer models
Anticancer Agents Med. Chem.
14
1031-1041
2014
Homo sapiens (Q9UHK6)
Manually annotated by BRENDA team
Autio, K.J.; Schmitz, W.; Nair, R.R.; Selkaelae, E.M.; Sormunen, R.T.; Miinalainen, I.J.; Crick, P.J.; Wang, Y.; Griffiths, W.J.; Reddy, J.K.; Baes, M.; Hiltunen, J.K.
Role of AMACR (aloha-methylacyl-CoA racemase) and MFE-1 (peroxisomal multifunctional enzyme-1) in bile acid synthesis in mice
Biochem. J.
461
125-135
2014
Mus musculus (O09174), Mus musculus, Mus musculus C57BL/6 (O09174)
Manually annotated by BRENDA team
Pal, M.; Easton, N.; Yaphe, H.; Bearne, S.
Potent dialkyl substrate-product analogue inhibitors and inactivators of alpha-methylacyl-coenzyme A racemase from Mycobacterium tuberculosis by rational design
Bioorg. Chem.
77
640-650
2018
Mycobacterium tuberculosis
Manually annotated by BRENDA team
Yang, D.K.; Chen, L.C.; Lee, M.Y.; Hsu, C.H.; Chen, C.S.
Selection of aptamers for fluorescent detection of alpha-methylacyl-CoA racemase by single-bead SELEX
Biosens. Bioelectron.
62
106-112
2014
Homo sapiens
Manually annotated by BRENDA team
Yevglevskis, M.; Lee, G.L.; Threadgill, M.D.; Woodman, T.J.; Lloyd, M.D.
The perils of rational design - unexpected irreversible elimination of fluoride from 3-fluoro-2-methylacyl-CoA esters catalysed by alpha-methylacyl-CoA racemase (AMACR; P504S)
Chem. Commun. (Camb.)
50
14164-14166
2014
Homo sapiens
Manually annotated by BRENDA team
Xu, B.; Cai, Z.; Zeng, Y.; Chen, L.; Du, X.; Huang, A.; Liu, X.; Liu, J.
alpha-Methylacyl-CoA racemase (AMACR) serves as a prognostic biomarker for the early recurrence/metastasis of HCC
J. Clin. Pathol.
67
974-979
2014
Homo sapiens
Manually annotated by BRENDA team
Yevglevskis, M.; Lee, G.; Sun, J.; Zhou, S.; Sun, X.; Kociok-Koehn, G.; James, T.; Woodman, T.; Lloyd, M.
A study on the AMACR catalysed elimination reaction and its application to inhibitor testing
Org. Biomol. Chem.
14
612-622
2015
Homo sapiens
Manually annotated by BRENDA team
Abbas, M.; Ploch, E.M.; Wehling, J.; Schipper, E.; Janciauskiene, S.; Kreipe, H.H.; Jonigk, D.
alpha-Methylacyl-coenzyme A racemase (AMACR, p504s) is a marker to distinguish malignant melanomas from dysplastic nevi and melanocytic nevi
Tumour Biol.
35
12015-12020
2014
Homo sapiens
Manually annotated by BRENDA team